Enantioselective Total Synthesis of (–)-Myrifabral A and B

Fulton, Tyler J. and Chen, Anthony Y. and Bartberger, Michael D. and Stoltz, Brian M. (2020) Enantioselective Total Synthesis of (–)-Myrifabral A and B. Chemical Science, 11 (39). pp. 10802-10806. ISSN 2041-6520. PMCID PMC8162428. doi:10.1039/d0sc01141j. https://resolver.caltech.edu/CaltechAUTHORS:20200304-153439734

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Abstract

A catalytic enantioselective approach to the Myrioneuron alkaloids (−)-myrifabral A and (−)-myrifabral B is described. The synthesis was enabled by a palladium-catalyzed enantioselective allylic alkylation, that generates the C(10) all-carbon quaternary center. A key N-acyl iminium ion cyclization forged the cyclohexane fused tricyclic core, while vinyl boronate cross metathesis and oxidation afforded the lactol ring of (−)-myrifabral A. Adaptation of previously reported conditions allowed for the conversion of (−)-myrifabral A to (−)-myrifabral B.

Item Type:

Article

Related URLs:

URL	URL Type	Description
https://doi.org/10.1039/d0sc01141j	DOI	Article
http://www.rsc.org/suppdata/d0/sc/d0sc01141j/d0sc01141j1.pdf	Publisher	Supplementary Information
https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8162428	PubMed Central	Article
https://doi.org/10.26434/chemrxiv.11900331.v1	DOI	Discussion Paper

ORCID:

Author	ORCID
Fulton, Tyler J.	0000-0002-9343-2456
Chen, Anthony Y.	0000-0002-9578-4893
Bartberger, Michael D.	0000-0002-5167-3139
Stoltz, Brian M.	0000-0001-9837-1528

Additional Information:

© 2020 The Royal Society of Chemistry. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. All publication charges for this article have been paid for by the Royal Society of Chemistry. Submitted 26 Feb 2020; Accepted 20 Apr 2020; First published 21 Apr 2020. We thank NIH-NIGMS (R01GM080269) and Caltech for financial support. Dr Scott Virgil (Caltech) is thanked for instrumentation and SFC assistance. We thank Dr David Vander Velde (Caltech) for NMR expertise, and Dr Mona Shahgholi (Caltech) and Naseem Torian (Caltech) for mass spectrometry assistance. There are no conflicts to declare.

Funders:

Funding Agency	Grant Number
NIH	R01GM080269
Caltech	UNSPECIFIED

Subject Keywords:

myrifabral; myrioneuron; Alkaloids; total synthesis; allylic alkylation

Issue or Number:

PubMed Central ID:

PMC8162428

DOI:

10.1039/d0sc01141j

Record Number:

CaltechAUTHORS:20200304-153439734

Persistent URL:

https://resolver.caltech.edu/CaltechAUTHORS:20200304-153439734

Official Citation:

Enantioselective Total Synthesis of (–)-Myrifabral A and B. Chem. Sci., 2020, 11, 10802-10806; doi: 10.1039/d0sc01141j

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No commercial reproduction, distribution, display or performance rights in this work are provided.

ID Code:

101714

Collection:

CaltechAUTHORS

Deposited By:

Tony Diaz

Deposited On:

04 Mar 2020 23:45

Last Modified:

07 Jun 2021 20:31

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